I've done only a small amount of web-design work over the years, but I can imagine that, if I landed on CSS-tricks trying to work out a tricky (to me) CSS or usability problem where LLMs had been failing me, and I had a quick and easy option to pay a few hundred dollars and meet with the guy who wrote the book, I might do that. That's also how I got a lot of my first customers in my current business; I offered paid phone calls where a user could pay a nominal rate and ask some upfront questions about a project they were working on. Many of those calls turned in to longer contracts, and the fee kept out the folks who were just looking to sell me something.
A lot of my customers have been organizations whose focus is not my industry, but, for one reason or another, they needed something done that fits in my wheelhouse. This means they don't (yet) want to hire this expertise and build processes internally, so they're willing to pay my premium rates. Perhaps there is a way to target these types of companies with custom services in the space.
The free one gets people in the door. Cheap is could be something like a book or paid tool or course. And the "expensive" would usually be consulting but could also be a more premium tool or retainer service.
So your suggestion seems to fit the model.
I know LLMs will change the developer education landscape but I really hope it doesn't kill it. Interesting times.
It might be interesting to have a list/map of WISPs on your site!